Palladium-Catalyzed Cross-Coupling Reaction of Organoindiums with Aryl Halides in Aqueous Media

Organic Letters

Volumn 3, Issue 13, 2001, Pages 1997-1998

  Takami, Kazuaki ^a   Yorimitsu, Hideki ^a   Shinokubo, Hiroshi ^a   Matsubara, Seijiro ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

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EID: 0005799777     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015975i     Document Type: Article

References (28)

1. (a) Metal-Catalyzed Cross-Coupling Reactions; Diedrich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
2. (b) Heck, R. F. Palladium Regents in Organic Syntheses; Academic Press: New York, 1985.
3. (c) Tsuji, J. Palladium Reagents and Catalysts. Innovations in Organic Synthesis; Wiley: Chichester, U.K., 1996.
4. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
5. (b) Suzuki, A., in ref 1a, Chapter 2.
6. (a) Pérez, I.; Pérez Sestelo, J.; Sarandeses, L. A. Org. Lett. 1999, 1, 1267-1269.
7. (b) Gelman, D.; Schumann, H.; Blum, J. Tetrahedron Lett. 2000, 41, 7555-7558.
8. (c) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4095-4101.
9. (d) Hirashita, T.; Yamamura, H.; Kawai, M.; Araki, S. Chem. Commun. 2001, 387-388.
10. (e) Pérez, I.; Pérez Sestelo, J.; Sarandeses, L. A. J. Am. Chem. Soc. 2001, 123, 4155-4160.
11. (a) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Son: New York, 1997.
12. (b) Grieco, P. A. Organic Synthesis in Water; Blackie Academic & Professional: London, 1998.
13. (c) Lubineau, A.; Auge, J. In Modern Solvents in Organic Synthesis; Knochel, P., Ed.; Springer-Verlag: Berlin Heidelberg, 1999.
14. Review on the use of indium in organic synthesis; Cintas, P. Synlett 1995, 1087-1096.
15. (a) Li, C.-J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017-7020.
16. (b) Araki, S.; Jin, S.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736-1738.
17. (a) Chan, T.-H.; Li, C.-J. J. Chem. Soc., Chem. Commun. 1992, 747-748.
18. (b) Li, C.-J. Chem. Rev. 1993, 93, 2023-2035.
19. For reviews on transition metal-catalyzed coupling reactions in aqueous media, see refs 4a, Chapter 5.5, and 4c, Chapter 2.
20. Palladium-catalyzed Ullmann-type reductive coupling reaction of aryl halides was reported: Venkatraman, S.; Li C.-J. Org. Lett. 1999, 1, 1133-1135.
21. 3 (0.01 mmol) and trifurylphosphine (0.06 mmol) in THF (1 mL).
22. Without water, 2.82 mmol of 2a was obtained.
23. It is not clear that diphenyindium hydroxide was formed. Tetraphenylindoxane or other oligomeric forms might be produced. However, throughout this text, we describe the compound as diphenyindium hydroxide for convenience.
24. See Supporting Information.
25. We also checked the formation of diphenylindium hydroxide from diphenylindium chloride on exposure to water. See Supporting Information.
26. Trifurylphosphine was the best among the ligands examined. Three equimolar amounts of phosphine to palladium were necessary. The use of one, two, or four equimolar amounts of trifurylphosphine gave 2a in 56%, 71%, or 65% yield, respectively, in the reaction of 1a with diphenylindium.
27. The reaction was sluggish when performed at ambient temperature. Treatment of 1a with diphenylindium at 25 °C for 24 h provided 2a in 14% yield.
28. 3 was essential to reproduce the yield of the coupling product. It is worth noting that other reactions shown in Table 1 did not require any bases. The effect of a base in the case of 1i is not clear at this stage.